HCID 22132580, compound → HCID 22132584, compound

HRID 1856770Notes

Reaction equation

HRID 1856770 reaction equation
[CH:1]1([N:7]([CH3:29])[C:8](=[O:28])[N:9]([CH2:13][CH2:14][CH2:15][O:16][C:17]2[CH:18]=[C:19]3[C:24](=[CH:25][CH:26]=2)[NH:23][C:22](=[O:27])[CH:21]=[CH:20]3)[CH2:10][CH:11]=[CH2:12])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[H][H]>C(O)C.[C].[Pd]>[CH:1]1([N:7]([CH3:29])[C:8](=[O:28])[N:9]([CH2:13][CH2:14][CH2:15][O:16][C:17]2[CH:18]=[C:19]3[C:24](=[CH:25][CH:26]=2)[NH:23][C:22](=[O:27])[CH:21]=[CH:20]3)[CH2:10][CH2:11][CH3:12])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 22132580HCID 22132580, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 22132584HCID 22132584, compoundYield 69.6%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

6-[3-(3-Cyclohexyl-3-methyl-1-allylureido)propoxy]carbostyril (3.0 g) is dissolved in ethanol (90 ml), and thereto is added 10% palladium-carbon (0.3 g), and the mixture is subjected to catalytic hydrogenation under 1 atm of hydrogen gas at room temperature. After the reaction is complete, the catalyst is removed by filtration, and the filtrate is concentrated under reduced pressure. The residue is purified by silica gel column chromatography (solvent; methylene chloride:methanol=20:1), and recrystallized from ethanol-diethyl ether to give 6-[3-(3-cyclohexyl-3-methyl-1-propylureido)propoxy]carbostyril (2.1 g) as colorless flakes.

Workup

  1. customthe catalyst is removed by filtration
  2. concentrationthe filtrate is concentrated under reduced pressure
  3. customThe residue is purified by silica gel column chromatography (solvent; methylene chloride:methanol=20:1)
  4. customrecrystallized from ethanol-diethyl ether

Sources & evidence

ORD record
ord-0e99a3fd019741a488356023c5b7f04a
Source dataset
uspto-grants-2000_11
Patent number
US06143763

Reaction notes

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